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Oak Park Bungalow. This charming Oak Park Bungalow offers a quiet relaxing environment to unwind after a busy day of site seeing in Chicago or enjoying the historic beauty of Oak Park.
The home has been divided into two units. The top two floors (Duplex) are the rental space above a garden...

Come relax in OAK PARK (OP) after a long day of shopping on Michigan Avenue, sightseeing in Chicago, or family gatherings. Just 10 minutes from downtown Chicago, Oak Park, and our flat offers the best of both worlds at a price you can afford. Just blocks from 2 train lines to Chicago. Pristine,...

At this Sonder, you&#39;ll love the beautiful fireplace, spacious balcony, and a fully-equipped kitchen. Located in Lakeview, know for its delicious dining and relaxed cafes.
Every booking is instantly confirmed. Every call or message is answered within minutes. Every home is equipped with crisp...

At this Sonder, you&#39;ll love the stunning architectural details, luxurious hardwood floors, and a spacious balcony. Located in Lakeview, known for its amazing eateries and relaxed cafes.
Every booking is instantly confirmed. Every call or message is answered within minutes. Every home is equipped...

At this Sonder, you&#39;ll love the expansive living area, sleek hardwood floors, and fully-equipped kitchen. Located in Roscoe Village, known for its hip boutiques and assortment of delicious restaurants.
When you stay at a Sonder, you have a 24/7 concierge and receive all the local color of a...

The house is an en-suite with 7 rooms, namely; living room, dining room, 2 bedrooms/lounge area, kitchen, two baths/toilets, nice decks and more, if you need room, this is the ideal spot for you and your guests.
A few blocks from the Metra Station as well as buses to take you directly to the...

When traveling and looking for an upscale location. Oak Park offer a great traveler great food, entertainment, relaxing environment. Safe and a wide array of guided tours, Frank Lloyd Widget homes is just the start. My condo has two room with king bed half bath master bedroom, 2 bedroom has queen...

Spacious 1 bedroom suite with a big screen TV, a super comfy bed &amp; the convenience of cooking your own meals (oven, frig &amp; microwave in your kitchen). Located on a wonderfully quiet residential block, very close to public trans and expressway. Downtown Chicago &amp; O&#39;Hare airport are one train ride...

Long modern open concept. New Renovation. Entire flat. Completely remodeled 3 bedroom 1.5 bath. Centrally located 15 min from O&#39;hare Airport, and 20 min from Downtown at non traffic hours with easy access to the highways. This entire Melrose Park apartment flat near the 25th Ave &amp; Lake St. features...

Adeline&#39;s Sea Moose hosts over night stays for yacht enthusiasts! This 68 ft luxury charter yacht is one of the few sizable multi-level private Charter yachts in Chicago, and that was built and has maintained a true private yacht. Great care has been taken to uphold the integrity of her styling....

Beautiful Oak Park, IL home of Earnest Hemingway and Frank Lloyd Wright. We boast beautiful homes, superb restaurants, shops and we are next door to Chicago a world class city!!
Welcome to my home where you will find comfortable beds, refreshments, conversation and a warm feeling of being...

The Map in the ad is wrong and Trip Advisor can&#39;t fix it. We are located in the Bridgeport neighborhood just south of downtown Chicago and just West of Guaranteed Rate Field, home of the Chicago White Sox.
We are located 5 miles due south from our city center, and 3 miles from our convention...

Hull Chateau is a delightful, bright, relaxed place. Hull Chateau is quiet and private. Guests will feel like home.
The entire house is open to guests. We Provide the guests the experience of a &#39;Home away from home&#39;.
Hull Chateau is in a great Evanston neighborhood. Quiet, peaceful, and...

This home is perfect if you want to be close to the airports and still have access to go downtown as well. You will love staying in this fully furnished and equipped home that will give you the experience as if you were staying at a place out of a modern home magazine. The TV is a smart TV with...

The Pinewoods Retreat is home to a small artist community including musicians, painters and acrobats. Here you will find an eclectic yet quiet escape from the fast paced city. We take great pride in the peaceful environment that we have created here and welcome you to share in our retreat.
Please...

Built in 1919, this elegant 4BR/3.5BA has been beautifully updated and features gleaming hardwood floors, stylish furniture, and tasteful art. Spread out in 3,300 square feet of comfortable living space, including two living rooms and a fenced backyard.
A fantastic location in Albany Park puts you...

Excitement bustles around Chicago as you approach this 2-bedroom, 2.5-bathroom vacation rental townhome! With room to host 4 on beds and other sleeping arrangements, this 3-story home offers 2 living areas, a gourmet kitchen, 2-car garage, and sophisticated decor, creating a luxury accommodation in...

This is a clean, quiet and cozy apartment in an amazing area that is perfect whether you are venturing locally or traveling downtown. Located off Irving and Cumberland you are within walking distance of multiple amazing bars and restaurants and a short drive from some of the best restaurants in the...

This incredibly lavish 2BR apartment boasts an array of antique furniture and fixtures. Rich wall paneling, sculptures, and fine furnishings make this Andersonville getaway truly unique. Step back in time while enjoying the modern convenience of a full contemporary kitchen.
Wrigleyville is a...

Planning a visit to Chicago? A Chicago vacation rental is a great hotel alternative. From modern apartments on the Magnificent Mile to cozy coach houses in Lincoln Park and everything in between, we’ve got a wide variety of Chicago vacation rentals so there’s sure to be one that’s just right for you. Whatever your budget, we’ll help you find a great deal. Plus, you can book with confidence - we have plenty of unbiased user reviews of Chicago vacation rentals!

Chicago family vacations

Chicago is a great city for families and a vacation home rental makes it easy to explore all that the second city has to offer. If it’s baseball season, catch a Chicago Cubs game at historic Wrigley Field, one of the oldest ball parks in the country. Or take the kids out to Navy Pier, which features amusement rides, shops and restaurants right on Lake Michigan. If you’re kids are animal lovers, visit the Great Ape House at the Lincoln Park Zoo, where admission is still free. Or see dinosaurs at The Field Museum of Natural History.

Chicago attractions

There's plenty to do in Chicago and a vacation rental in the city will put you within walking distance of most of the city's many attractions. Art lovers will enjoy the Art Institute of Chicago where they can browse the large collection of impressionist and post-impressionist paintings before heading to the newer Modern Wing. After, you’ll want to head over to nearby Millennium Park, which features public art and cultural events year-round. During the warmer months, find a spot on the sand at Oak Street Beach, a great place to people watch with views of downtown skyscrapers and Lake Michigan.

Chicago day trips

For those who want to explore Chicago beyond the city center, there are plenty of short getaways worth exploring, all within an hour or two of your vacation rental. Nearby Oak Park is home to the Frank Lloyd Wright Home and Studio. It’s also the birthplace of Ernest Hemingway. For those looking for outdoor adventure, head south to Starved Rock State Park where you can hike miles of trails through rolling hills or go fishing, boating or horseback riding. Other popular getaways include Lake Geneva in southern Wisconsin or the shores along Lake Michigan outside the city.

Saving money on Chicago vacation rentals

Whether you want to stay in a chic downtown apartment rental in Chicago or a spacious house in the suburbs, we can help you find a deal that fits your budget. There are discounts on every type of property to help you get the most bang for your buck.

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